Sodium Carbonate → (4-Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

HRID 1867501Notes

Reaction equation

HRID 1867501 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:10]=1)=[N:7][O:8][N:9]=2.C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][N:18]([CH3:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>COCCOC.O>[N:9]1[O:8][N:7]=[C:6]2[CH:10]=[C:2]([C:22]3[CH:23]=[CH:24][C:19]([N:18]([CH3:28])[CH3:17])=[CH:20][CH:21]=3)[CH:3]=[CH:4][C:5]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 27762985-Bromo-2,1,3-benzoxadiazole

Product 1

HCID 11687340(4-Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

500 mg (2.5 mmol) 5-bromo-benzo[1,2,5]oxadiazole and 313 mg (0.1 eq.) tetrakis-(triphenylphosphine)palladium are stirred for 30 minutes at room temperature in 10 mL 1,2-dimethoxyethane. 533 mg (2 eq.) sodium carbonate are dissolved in 1.8 mL water and added to the reaction mixture, followed by 663 mg (1.6 eq.) 4-(dimethylamino)phenylboronic acid. After stirring at reflux for 18 h, the reaction mixture is cooled to room temperature and extracted with ethyl acetate and water. The organic phases are combined, dried with magnesium sulfate, filtered and evaporated. The residue is column chromatographed (hexane, then hexane/ethyl acetate 8:1 then 5:1) to yield the desired product as a yellow solid. MS(ES+): 240 (M+1).

Workup

  1. additionadded to the reaction mixture
  2. temperatureat reflux for 18 h
  3. extractionextracted with ethyl acetate and water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed (hexane

Sources & evidence

ORD record
ord-e5fe52ffd71f4cf6a11c6c8e981ea378
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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